Lithium Hydroxide → 2-(difluoromethyl)-1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylic acid

HRID 1749644노트

반응식

HRID 1749644 반응식
[F:1][CH:2]([F:34])[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[C:10]=2[CH3:19])[C:6]2[CH:20]=[C:21]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[CH:22]=[C:23]([C:24]([O:26]C)=[O:25])[C:5]=2[N:4]=1.[Li+].[OH-]>C1COCC1>[F:34][CH:2]([F:1])[C:3]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[C:10]=2[CH3:19])[C:6]2[CH:20]=[C:21]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[CH:22]=[C:23]([C:24]([OH:26])=[O:25])[C:5]=2[N:4]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 66977078methyl 2-(difluoromethyl)-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate

생성물 1

HCID 569606852-(difluoromethyl)-1-{[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylic acid수율 59%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
45 °C

실험 절차

A mixture of methyl 2-(difluoromethyl)-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-morpholino-1H-benzo[d]imidazole-4-carboxylate (700 mg, 1.45 mmol) and 2 N LiOH (5 mL) in THF (10 mL) was stirred at 45° C. for 4 h. It was filtered, the filter cake was dissolved in water (10 mL) and formic acid was added to adjust pH=3-4. Then a filtration was performed and the filter cake was dried under vacuum to give the desired product (400 mg, 59%) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.53 (s, 3H), 3.13 (s, 4H), 3.73 (s, 4H), 5.75 (s, 2H), 6.29 (d, 1H, J=7.5 Hz), 7.19-7.61 (m, 5H), 12.97 (br s, 1H); LC-MS: m/e=470 [M+1]+

후처리

  1. filtrationIt was filtered
  2. dissolutionthe filter cake was dissolved in water (10 mL)
  3. additionformic acid was added
  4. filtrationThen a filtration
  5. customthe filter cake was dried under vacuum

출처 및 근거

ORD 기록
ord-7078f3b24ffc4039affeae81e607b071
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156797B2

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